Synthesis and Structural Analysis of Some New Sulfanyl Amino 1,4-Naphthoquinone Derivatives

Authors : Hatice YILDIRIM

Pages : 149-158

Doi:10.18596/jotcsa.335894

View : 12 | Download : 8

Publication Date : 2017-09-01

Article Type : Research Paper

Abstract :In this study, some new sulfanyl substituted amino 1,4-naphthoquinone derivatives which possess two electron donating groups in the amino fragment were synthesized and their structures were analyzed by spectroscopic techniques. First, 2-chloro-3-[insert ignore into journalissuearticles values(2,4-dimethoxy phenyl);amino]naphthalene-1,4-dione insert ignore into journalissuearticles values( 3a ); and 2-chloro-3-[insert ignore into journalissuearticles values(3,5-dimethoxy phenyl);amino]naphthalene-1,4-dione insert ignore into journalissuearticles values( 3b ); were obtained from the reactions of dichloro 1,4-naphthoquinone insert ignore into journalissuearticles values( 1 ); with 2,4-dimethoxy phenyl amine and 3,5-dimethoxy phenyl amine. Then the compounds 3a , b were reacted with aliphatic nucleophiles; ethyl-, propyl- and pentyl mercaptan. S-Nucleophiles attacked to the carbon atom of 1,4-naphthoquinone core and displaced with the chlorine atom to create target molecules; 2-aryl amino- 3 -insert ignore into journalissuearticles values(ethyl thio);naphthalene-1,4-dione insert ignore into journalissuearticles values(5a,b); , 2-aryl amino-3-insert ignore into journalissuearticles values(propyl thio);naphthalene-1,4-dione insert ignore into journalissuearticles values(5c,d); , 2-aryl amino-3-insert ignore into journalissuearticles values(pentyl thio);naphthalene-1,4-dione insert ignore into journalissuearticles values(5e,f); derivatives. The structures of synthesized compounds were proved by utilizing 1D and 2D NMR techniques and also mass spectra and FTIR data.
Keywords : Sulfanyl and or arylamine substituted quinones, 1, 4 naphthoquinone, spectroscopic analysis, HMQC HMBC analysis